When it comes to money, there’s a certain amount of fear that is ingrained in us as we grow up. We are taught early on that we need a good education to get a good job to make a good living to pay for a good home in a good neighborhood and provide a secure future for ourselves and our family. To do this, we need health insurance and life insurance and stocks and bonds and savings accounts and IRAs. When we can’t provide these things – or find that what we’re most passionate about in life just doesn’t provide these things – then that fear grows stronger, even paralyzing at times.

I believe that fear is irrational.

See how cute he is??

All my life I was afraid of spiders. Everyone I knew was afraid of them too, from my friends at school to my own parents. Having arachnophobia just seemed so normal, I never questioned it. Then one day, as I was taking a nap on the back porch, I felt something crawling up my arm. I looked down to see a hairy little wolf spider. I wanted to freak out. I mean, I was supposed to freak out, right? The only thing was, I had fallen asleep with my laptop in my lap and any sudden movement would have sent it sailing. So, I sat for a second, just me and the spider. He stopped. I stared. He was so small and well, kind of cute, and even if he had teeth, it wasn’t likely that he was going to chew me up like a wolverine. In that moment, I realized, there was no logical reason for me to be afraid. I didn’t have to do what everyone else did. And who knows, I might even like spiders (or at least some of them).

The same thing happened for me with money. All my life I subscribed to the same fears as my friends and family. I fought viciously to keep up. I racked up student loans to pay for a degree I’ve never used. I took out a zero-down mortgage because “successful people don’t waste their money on rent”. Never mind that part of it was on a 5-year ARM. I bought stuff. I had debt. But I was living the dream, according to those same friends and family. Until I wasn’t. When the economy collapsed, I lost my home. In the months that followed, I liquidated my savings, sold what I could of my possessions to cover my debts, and still ended up filing bankruptcy. Was it something I wanted to do? Absolutely not. Was it the worst thing that ever happened to me? Not even close.

If you’ve never filed bankruptcy, you may not know this, but the first things that you start to get – almost the minute that you leave the courthouse – are credit card offers. It seems counter-intuitive, but it actually happens. Next come the car loan solicitations. From the minute you are free of debt, someone is trying to put you back in it; because this is the way our society works. You are a financial failure if you don’t get back up on the debt pony.

I don’t consider myself a financial failure. I was just unsuccessful at living the American Dream. Why? Because it was never mine in the first place. When I lost everything I owned, a great thing happened. For the first time in my life, my so-called friends and family stopped telling me what to do (most stopped talking to me altogether, at least for a while) and I was left to figure things out on my own – in my own time, in my own way.

I paid off my last post-bankruptcy debt in 2009, while I was living with friends and driving a beat-up Jeep to a job 45 miles away making $11 an hour. I won’t lie and say that it was easy or that I was happy. Happiness didn’t come until much later. What I was back then was focused, but not on the things you might think. I wasn’t focused on rebuilding my credit score or getting back the lifestyle I was “accustomed” to. I was focused on figuring out what really mattered to me.

Bankruptcy didn’t teach me the value of money. It didn’t make me want to earn back all that I had lost and hold onto it for dear life. It taught me that money doesn’t matter much at all in the end. With or without it, I was still the same person, but without it, the world held so much more potential. I didn’t have to live by “the rules” and be afraid of financial failure anymore. I had already failed, but more importantly, I had survived.

It’s a decade later and I believe I have a pretty good handle on what matters most in my life, but my financial recovery has put me right back in the same position with my friends and family that I was before bankruptcy. I get a lot of unsolicited advice and there are some close family members who still give me grief about not owning a home (though I can successfully argue the merits of renting); not getting an advanced degree (In what? Student loans?); and not having a “meaningful” career (which actually means “lucrative” because I’m pretty sure helping non-profits find funding for programs that keep homeless youth off the streets and hungry seniors fed is pretty meaningful). Though I know better, the constant bombardment of other people’s opinions can wear on me and I start to think, maybe I’m not doing the right things. Maybe I do need to buy a house. Maybe I do need to work harder to save more for retirement. Maybe I’m not measuring up to where I should be by this age.

Then I remember: I’m no longer afraid of spiders.

How have your financial failures (or successes) shaped your life to this point? Do your friends and family offer you well-meaning but unwanted financial advice? If so, how do you handle it?

A few weeks ago, the strangest thing happened. We were visiting with my mom, when my uncle called. He is the youngest of my mom’s siblings at 58 years old. They have always been close, even though they fight like cats and dogs much of the time; so, when she answered the phone, I gathered up my stuff to leave and let them talk. As I was waving goodbye, I heard her say, “Yes, she’s here. I’m not sure, you’ll have to ask her yourself.” The next thing I knew, I was on the phone with my uncle.

For the record, I don’t share my mom’s sentiments when it comes to my uncle. I tolerate him and am always nice to him, but we’ve never had much of a relationship. When I was growing up, he would go on rants and put his fist though the wall or block people from leaving the room until he was finished talking. I later learned that he was an addict at that time; but as a child, his behavior terrified me. Though he has not used drugs for 20+ years now, his personality has never really mellowed. He might not put his fist through walls anymore, but he still goes on rants that make you wish you could crawl under the furniture and disappear. He won’t talk to one of his daughters because of the way she voted in the last presidential election and his 13-year old son told me that he’d rather be dead than live with his dad. And here I was on the phone with him.

Over the past few years, I’ve talked to him a few times on his visits to see my mom. Once he was contemplating opening a community center and wanted my help in setting up a 501c3. I directed him to see a lawyer. As I held the phone, I thought perhaps he was going to ask me to write a grant to help fund his venture. In my mind, there was no other possibility for why he would want to talk to me. Then he asked me to be the trustee of his estate.

I had to let that sink in for a minute, which was pretty easy to do since he never stopped talking long enough for me to answer. As a fog settled around my brain, I caught snippets of things like money in a safe deposit box, envelopes with people’s names on them in the office safe, real estate taxes, and investing something for someone to do something with sometime. I wanted to scream. I am the last person who wants to be responsible for someone else’s finances.

If you are unsure (like I was) what the role of a trustee is, let’s look at it together. According to the website for the Law Offices of John W. Callinan:

A trustee is responsible for investing and administering the assets of the trust. A trustee can be held liable to the beneficiaries of the trust if he invests the assets of the trust in an imprudent manner. A trustee must also distribute the assets of the trust to the beneficiaries of the trust according to the terms of the trust. The role of trustee may last for several months or several decades. So, unlike an executor, a trustee may be serving in his role for a long, long time.

When he finished talking, I gave him the best answer that I could muster: I’ll think about it. In the weeks that have followed, I’ve thought about it…and thought some more…but never once have I thought about saying yes.

I can’t do this.

When my uncle dies, his wife and kids will fight over his estate. I know this because they fight over it now and he rewards (or punishes) this behavior by giving (or withholding) money. Right now, my aunt owes more than $30,000 on her credit card. This is her 3rd time in the last decade to amass this amount of consumer debt. When my uncle wants her to do something, like quit her job or move back in after a separation, he offers to pay off her debt in full. She always accepts, then racks up the debt again. Same for the younger kids, except his bribes to them are in the form of gadgets and games, which I’ve watched them purposely break in order to get newer, better ones. And the madness doesn’t stop there. In the mid-90s, before my uncle got clean, he borrowed a total of $5,000 from 3 of his siblings to make payroll for his home-improvement business. He has never repaid those debts, despite having the money to do so many times over, and he makes a special point when any of them asks for financial help to tell them that he owes them nothing because “they had no business loaning money to an addict in the first place”.

Witnessing behavior like this is part of the reason that I have such an aberrant view of money. It makes me sad and angry and sick, all at the same time, to see people abuse one another all for the sake of a green piece of paper! I can’t be his trustee. I can’t be a part of something that goes against everything I believe in, on so many levels.

I wish that I could say that this type of behavior is rare but I’m not sure that it is. I once watched two sisters fight over who was taking home more plants at their father’s funeral. I also witnessed a grandchild throw a screaming fit at a funeral visitation because her dead grandfather had left his house to his oldest son instead of her. Angie even recalls a time when her nephew told her dad that he wished he was dead so he could get his inheritance and many more times where her siblings have had serious discussions with their parents about spending up all their money. I bet if you really thought about it, you know someone like this too. I hate that we’ve come to a place in this world where the sum of someone’s life means less than what we can gain from their death.

When my mom passes, I hope that she has lived a long, happy life unconcerned about what possessions she will leave behind. I honestly hope that she has spent ever last dime that she saved for her retirement by then. Her legacy gift to me should be the time we spend together while she’s here, not an insurance policy or a safe deposit box full of cash.

I ultimately told my uncle no. I gave no explanation other than that I thought it was a lot to ask and I didn’t think that I could do it. Perhaps that’s a cop out. Perhaps I should have told him how nauseous I felt just considering it, but I doubt it would have made any difference. I am never going to change the way he thinks about money. I can only change myself, and more than anything, this incident has confirmed for me that money is the least important part of my life.

Want to know what is important? Spending time together. Be sure to keep up with out latest adventures in dating through our 48 Really Great Dates project.